Rishitin

Base Information

• Chemical Name: Rishitin
• CAS No.: 18178-54-6
• Molecular Formula: C₁₄H₂₂O₂
• Molecular Weight: 222.327
• UNII: FQY1K3HR10
• DSSTox Substance ID: DTXSID60171184
• Nikkaji Number: J13.920C
• Wikipedia: Rishitin
• Wikidata: Q27108165
• Metabolomics Workbench ID: 68097
• Mol file: 18178-54-6.mol

Synonyms:rishitin;rishitin, (1S-(1alpha,2beta,3alpha,7beta))-isomer

Chemical Property of Rishitin

Chemical Property:

• Vapor Pressure: 4.48E-06mmHg at 25°C
• Boiling Point: 343.5°Cat760mmHg
• Flash Point: 158.5°C
• PSA: 40.46000
• Density: 1.07g/cm³
• LogP: 2.42080
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 222.161979940
• Heavy Atom Count: 16
• Complexity: 330

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(CC2=C1CC(CC2)C(=C)C)O)O
• Isomeric SMILES: C[C@@H]1[C@H]([C@@H](CC2=C1C[C@@H](CC2)C(=C)C)O)O

Technology Process of Rishitin

There total 12 articles about Rishitin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

[(4R,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]methanol (114817-96-8) → (-)-rishitin (18178-54-6)

Guidance literature:

Multi-step reaction with 7 steps

1: Swern oxidation

2: MeLi

3: 1.) H(+); 2.) CuH

4: NH₂NH₂

5: 1.) I₂, tetramethylguanidine; 2.) DBU / 2.) 90 deg C

6: yributyltin hydride, AIBN / toluene / Heating

7: H₃O(+)

With 2,2'-azobis(isobutyronitrile); 1,1,3,3-tetramethylguanidine; oxonium; methyllithium; iodine; tri-n-butyl-tin hydride; hydrogen cation; 1,8-diazabicyclo[5.4.0]undec-7-ene; copper(I) hydride; hydrazine; In toluene;

DOI:10.1016/S0040-4039(97)00228-1

Reference yield:

((R)-5-Isopropenyl-cyclohex-1-enyloxy)-trimethyl-silane (188568-00-5) → (-)-rishitin (18178-54-6)

Guidance literature:

Multi-step reaction with 6 steps

1: MeLi

2: 1.) H(+); 2.) CuH

3: NH₂NH₂

4: 1.) I₂, tetramethylguanidine; 2.) DBU / 2.) 90 deg C

5: yributyltin hydride, AIBN / toluene / Heating

6: H₃O(+)

With 2,2'-azobis(isobutyronitrile); 1,1,3,3-tetramethylguanidine; oxonium; methyllithium; iodine; tri-n-butyl-tin hydride; hydrogen cation; 1,8-diazabicyclo[5.4.0]undec-7-ene; copper(I) hydride; hydrazine; In toluene;

DOI:10.1016/S0040-4039(97)00228-1

Reference yield:

(3R,4R)-5-(tert-butyldimethylsiloxy)-3,4-(isopropylidenedioxy)pent-1-ene (188567-96-6) → (-)-rishitin (18178-54-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 80 percent / Bu₄NF

2: Swern oxidation

3: MeLi

4: 1.) H(+); 2.) CuH

5: NH₂NH₂

6: 1.) I₂, tetramethylguanidine; 2.) DBU / 2.) 90 deg C

7: yributyltin hydride, AIBN / toluene / Heating

8: H₃O(+)

With 2,2'-azobis(isobutyronitrile); 1,1,3,3-tetramethylguanidine; oxonium; tetrabutyl ammonium fluoride; methyllithium; iodine; tri-n-butyl-tin hydride; hydrogen cation; 1,8-diazabicyclo[5.4.0]undec-7-ene; copper(I) hydride; hydrazine; In toluene;

DOI:10.1016/S0040-4039(97)00228-1

upstream raw materials:

(3aR,4S,6R,9aR)-6-Isopropenyl-2,2,4-trimethyl-3a,4,5,6,7,8,9,9a-octahydro-naphtho[2,3-d][1,3]dioxole

2,3-O-isopropylidene-D-threo-4-pentenose

(2S,3R)-2,3-O-isopropylidene-1-O-p-tosyl-4-pentene-1,2,3-triol

[(4R,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]methanol

Downstream raw materials:

glutinosone

(+)-oxyglutinosone

13-hydroxyrishitin

Refernces

• 1、 Murai,A. et al.. "-". . p. 1206 - 1216. Retrieved 1977.